Our invention relates to 1-phenyl-1-cyano-C.sub.5 -C.sub.7 alkanes defined according to the structure: ##STR2## wherein R.sub.1 and R.sub.2 each represents hydrogen or methoxy with the proviso that when R.sub.1 is methoxy, R.sub.2 is hydrogen and when R.sub.2 is methoxy, R.sub.1 is hydrogen; and wherein X represents C.sub.3 -C.sub.5 straight chain or branched chain alkylene. Our invention also covers the specific compounds having the structures: ##STR3## as novel compounds. Our invention also covers the uses of the compounds defined according to the generic structure: ##STR4## for their organoleptic (e.g., perfumery) properties. Our invention also covers processes for preparing the compounds defined according to the generic structure: ##STR5## by means of reacting benzyl cyanide with an aldehyde or ketone and then hydrogenating the resulting product using a supported palladium catalyst.
There has been considerable work performed relating to substances which can be used to impart (modify, augment or enhance) fragrances to (or in) various consumable materials. These substances are used to diminish the use of natural materials some of which may be in short supply and to provide more uniform properties in the finished product.
Long-lasting, intense, and substantive floral, rose, muguet, herbal, green, fruity, pineapple-like, salicylate, basil, sweet, living orange flower, almond, cherry, woody, cigar box-like, ambergris, animalic, honey-like, musky, balsamic, cedarwood and sage-like aromas, with sweet, woody, fruity, wine-like, green, salicylate, animalic, honey-like, floral, rose, cabreuva oil-like and bois-de-rose topnotes, and sweet, green, floral, muguet, rose, salicylate, anethole-like, carvone-like, costus and almondy undertones and with a "cooling" effect on the skin on dry-out are highly desirable in several types of perfume compositions, perfumed articles and colognes (e.g., floral fragrances).
The perfume uses of nitrile-containing derivatives which contain phenyl moieties are well known in the prior art. Thus, the compounds defined according to the structure: ##STR6## wherein R.sub.1 and R.sub.2 are the same or different and each represents hydrogen or methyl are disclosed in U.S. Pat. No. 5,143,899 issued on Sep. 1, 1992 (title "Process For Preparing Phenyl Butyronitriles And Perfumery Use Of 2,2-Dimethyl-4-Phenyl Valeronitrile"). Other perfume uses of nitrile-containing derivatives which also contain phenyl moieties which are shown in U.S. Pat. No. 4,837,351 issued on Jun. 6, 1989 wherein it is indicated that the compound having the structure: ##STR7## has a powerful, fresh, fruity, floral odor note accompanied by a citrus, green topnote. Furthermore, U.S. Pat. No. 3,325,369 discloses the use of cinnamonitrile as a material useful in augmenting or enhancing the aroma of perfume compositions.
In addition, a mixture of the compounds having the structures: ##STR8## is marketed as TABACENE.RTM. by Firmenich et cie, S.A. of Geneva, Switzerland (as referred to in the Fragrance Materials Association of The United States, Inc. "Trademark And Coined Names Catalogue" on page T1). Nothing in the prior art however discloses the 1-phenyl-1-cyano-C.sub.5 -C.sub.7 alkanes of our invention having their unexpected, unobvious and advantageous uses in perfumery.
The Romanian Patent No. 75,279 abstracted at Chemical Abstracts Volume 99:139517m, 1983, discloses the reaction sequence: ##STR9## but does not set forth the unobvious, advantageous and unexpected results when using the conditions of the reaction sequence of our invention to prepare the 1-phenyl-1-cyano-C.sub.5 -C.sub.7 alkanes of our invention having the generic structure: ##STR10## which reaction sequence is: ##STR11## wherein R.sub.3 and R.sub.4 each represents hydrogen or lower alkyl with the proviso that R.sub.3 and R.sub.4 are not both hydrogen.